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Aldimines and ketimines as initiators in hardener systems and corresponding resin compositions inter alia for fixing technology

a technology of initiators and hardeners, which is applied in the field of hardener systems, can solve the problems of affecting the mechanical strength of paste-form hardener compositions, and affecting the mechanical strength of synthetic resin compositions, so as to achieve the effect of improving strength and bonding stresses, particularly effective hardener systems

Active Publication Date: 2020-01-28
FISCHERWERKE ARTUR FISCHER GMBH & CO KG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text describes the use of certain chemicals as initiator systems for synthetic resin compositions. Specifically, the use of aldehydes, ketones, and primary amines together with metal salts as initiator systems, and aldimines and ketimines in combination with metal salts, has been found to be effective. The use of these initiator systems results in stronger and more robust resin compositions with improved bond strength and a wider range of metal salts that can be used as accelerators.

Problems solved by technology

A disadvantage of those known initiator systems, however, is the use of peroxides as free-radical starter.
They are thermally sensitive and react sensitively to impurities, with the result that the formulation of paste-form hardener compositions is subject to considerable limitations in respect of storage temperature, storage stabilities and the choice of suitable constituents.
Acting as plasticisers, the latter significantly impair the mechanical strength of the synthetic resin compositions.
A disadvantage of reactive resin compositions according to EP 2 824 117 A1 is that they allow only low strengths or bond stresses and in some cases are classified as harmful (PMDETA is labelled with a skull and crossbones).

Method used

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  • Aldimines and ketimines as initiators in hardener systems and corresponding resin compositions inter alia for fixing technology
  • Aldimines and ketimines as initiators in hardener systems and corresponding resin compositions inter alia for fixing technology
  • Aldimines and ketimines as initiators in hardener systems and corresponding resin compositions inter alia for fixing technology

Examples

Experimental program
Comparison scheme
Effect test

example 1

orking Procedure I: Alternative Synthesis of Aldimines

[0100]The appropriate amine is placed in a round-bottomed flask. With vigorous stirring, the aldehyde is slowing added from a dropping funnel, during which the temperature of the mixture rises. Once the addition is complete, the volatile constituents are not removed. Depending upon the amine used (“hydrophobic” amines), the water of reaction that forms separates from the aldimine. The residual water present in the aldimine does not interfere with its use as initiator. Using “hydrophilic” amines, no phase separation takes place. If desired, it is also possible for the aldehyde to be used as initial charge and the amine to be added dropwise. The reaction (freedom from imine groups demonstrable by IR spectroscopy) is checked by means of FT-IR.

example 2

Formulation for an Aldimine from Isobutyraldehyde and Jeffamine D230

[0101]The formulation for an aldimine produced or producible according to Example 1 (general working procedure I) is as follows:

[0102]

TABLE 2Formulation for aldimine from isobutyraldehydeand Jeffamine D230Raw materialm [g]M [g / mol]n [mol]% by weightIsobutyraldehyde15.0072.110.20838.54D23023.92230.000.10461.46Total38.92100.00

[0103]The water of reaction that forms slowly separates from the aldimine and collects at the bottom of the flask.

[0104]The aldimines used below are produced analogously to general working procedure I, or are commercially available.

example 3

d Resin Formulations

[0105]For the simplified resin formulations the following raw materials are mixed together:

[0106]

TABLE 3Simplified resin formulation I (RFI)Raw material% by weightEthoxylated bisphenol-A-dimethacrylate*88.76BDDMA7.14HPMA4.10*technical product - various degrees of ethoxylation possible.

[0107]

TABLE 4Simplified resin formulation II (RFII)Raw material% by weightUM resin54.86BDDMA40.00HPMA5.00Additives0.14

[0108]The UM resin is produced in a manner known to the person skilled in the art. Reference is made here by way of example to the patent DE 4111828 A1. As isocyanate there is used a polymeric diphenylmethanediisocyanate with isomers and higher homologues.

[0109]

TABLE 5Simplified resin formulation III (RFIII)Raw material% by weightEthoxylated bisphenol-A-dimethacrylate*80.00SR21020.00*technical product - various degrees of ethoxylation possible.

[0110]The simplified resin formulation III is particularly interesting for the production of non-hazard-classified reactive r...

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Abstract

A hardener system for a synthetic resin composition having free-radical-polymerisable compounds, which includes the following constituents: a) at least one activator in the form of a metal salt, and as free-radical starter b1) (i) at least one aldehyde and / or ketone and at least one primary amine, and / or b2) (ii) at least one aldimine or (iii) at least one ketimine, or a mixture of two or more of constituents (i) to (iii). In addition, synthetic resin compositions having such a hardener system for application especially in fixing technology, and subject matters related thereto.

Description

TECHNICAL FIELD[0001]The invention relates to a hardener system, comprising (i) at least one aldehyde and / or ketone and at least one primary amine, (ii) at least one aldimine or (iii) at least one ketimine, or a mixture of two or more of the constituents (i) to (iii), and at least one activator (accelerator) in the form of a metal salt as initiator system for a synthetic resin composition that includes free-radical-polymerisable compounds, preferably suitable or adapted for use or for processes in chemical fixing technology; to a synthetic resin composition that includes such a hardener system, to the use of the hardener system or the synthetic resin composition, especially in the fixings field, and to associated further subject matters of the invention, such as processes, methods and uses.DISCUSSION OF RELATED ART[0002]Synthetic resin compositions based on free-radical-polymerisable (hardenable) compounds, such as unsaturated polyester resins and vinyl ester resins, are known as ad...

Claims

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Application Information

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IPC IPC(8): C08F4/26C09J5/00C09J4/00C09D4/00C04B41/48C08F4/20C08F4/10
CPCC09J5/00C08F4/20C09J4/00C08F4/10C04B41/483C08F4/26C09D4/00C08F2220/343C08F2222/102C08F2220/286C08F220/20C09J2433/00C09J2400/263C08F2222/1013C08F220/34C08F222/1006C08F220/343C08F222/1025C08F222/102C08F220/286
Inventor GRUEN, JUERGENSTEURER, PAULVOGEL, MARTINSCHLENK, CHRISTIANWEINELT, CHRISTIAN
Owner FISCHERWERKE ARTUR FISCHER GMBH & CO KG